Subtopic Deep Dive

Crystal Engineering of Cocrystals
Research Guide

What is Crystal Engineering of Cocrystals?

Crystal engineering of cocrystals designs multicomponent crystals using supramolecular synthons between active pharmaceutical ingredients and coformers to enhance solubility, stability, and bioavailability.

Research employs screening strategies, structural databases, and property prediction models. Over 500 papers exist on pharmaceutical cocrystals since 2000. Key advances include mechanochemical synthesis and halogen bonding applications (Bolla et al., 2022; Mukherjee et al., 2014).

15
Curated Papers
3
Key Challenges

Why It Matters

Cocrystals improve drug solubility without covalent changes, as shown in theophylline cocrystals enhancing physical stability (Trask et al., 2006, 548 citations). Carbamazepine forms 13 new phases via crystal engineering, addressing polymorphism issues (Fleischman et al., 2003, 530 citations). Explosives benefit from CL-20:HMX cocrystals with higher power and sensitivity (Bolton et al., 2012, 557 citations). Shan and Zaworotko (2008, 730 citations) highlight pharmaceutical applications for better bioavailability.

Key Research Challenges

Predicting cocrystal formation

Screening coformers for reliable synthon formation remains trial-intensive due to unpredictable intermolecular interactions. Computational models often fail for complex APIs (Bolla et al., 2022). Energy framework analysis aids but requires validation (Mackenzie et al., 2017).

Scalable green synthesis

Mechanochemistry reduces solvents but scales poorly for industrial production. Reaction control in ball mills varies with hardware (Howard et al., 2018, 908 citations). Purity and yield optimization challenges persist.

Property prediction accuracy

Solubility and stability forecasts from crystal structures lack precision for bioavailability. Halogen and other noncovalent bonds complicate models beyond hydrogen bonds (Mukherjee et al., 2014; Alkorta et al., 2020).

Essential Papers

1.

<i>CrystalExplorer</i>model energies and energy frameworks: extension to metal coordination compounds, organic salts, solvates and open-shell systems

Campbell F. R. Mackenzie, Peter R. Spackman, Dylan Jayatilaka et al. · 2017 · IUCrJ · 1.3K citations

The application domain of accurate and efficient CE-B3LYP and CE-HF model energies for intermolecular interactions in molecular crystals is extended by calibration against density functional result...

2.

Mechanochemistry as an emerging tool for molecular synthesis: what can it offer?

Joseph L. Howard, Qun Cao, Duncan L. Browne · 2018 · Chemical Science · 908 citations

Mechanochemistry is becoming more widespread as a technique for molecular synthesis with new mechanochemical reactions being discovered at increasing frequency. This perspective explores what more ...

3.

Halogen Bonds in Crystal Engineering: Like Hydrogen Bonds yet Different

Arijit Mukherjee, Srinu Tothadi, Gautam R. Desiraju · 2014 · Accounts of Chemical Research · 896 citations

The halogen bond is an attractive interaction in which an electrophilic halogen atom approaches a negatively polarized species. Short halogen atom contacts in crystals have been known for around 50...

4.

The role of cocrystals in pharmaceutical science

Ning Shan, Michael J. Zaworotko · 2008 · Drug Discovery Today · 730 citations

5.

High Power Explosive with Good Sensitivity: A 2:1 Cocrystal of CL-20:HMX

Onas Bolton, Leah R. Simke, Philip F. Pagoria et al. · 2012 · Crystal Growth & Design · 557 citations

A novel energetic cocrystal predicted to exhibit greater power and similar sensitivity to that of the current military standard explosive 1,3,5,7-tetranitro-1,3,5,7-tetrazacyclooctane (HMX) is pres...

6.

A systematic analysis of atomic protein–ligand interactions in the PDB

Renato Ferreira de Freitas, Matthieu Schapira · 2017 · MedChemComm · 550 citations

We compiled a list of 11 016 unique structures of small-molecule ligands bound to proteins representing 750 873 protein–ligand atomic interactions, and analyzed the frequency, geometry and the impa...

7.

Physical stability enhancement of theophylline via cocrystallization

A.V. Trask, W.D.S. Motherwell, W. Jones · 2006 · International Journal of Pharmaceutics · 548 citations

Reading Guide

Foundational Papers

Start with Fleischman et al. (2003) for multi-component phases of carbamazepine demonstrating synthon design; Shan and Zaworotko (2008) for pharmaceutical context; Trask et al. (2006) for stability enhancement examples.

Recent Advances

Bolla et al. (2022) reviews discovery and development; Mackenzie et al. (2017) extends CrystalExplorer to cocrystals; Howard et al. (2018) on mechanochemistry.

Core Methods

Supramolecular synthons (Desiraju via Mukherjee 2014); CE-B3LYP energy models (Mackenzie 2017); mechanochemical grinding (Howard 2018); halogen bonds (Mukherjee 2014).

How PapersFlow Helps You Research Crystal Engineering of Cocrystals

Discover & Search

Research Agent uses searchPapers and exaSearch to find cocrystal papers on carbamazepine, then citationGraph on Fleischman et al. (2003) reveals 530+ citing works. findSimilarPapers expands to Zaworotko collaborations like Shan et al. (2008).

Analyze & Verify

Analysis Agent applies readPaperContent to Bolla et al. (2022) for synthon details, verifyResponse with CoVe checks claims against Shan et al. (2008), and runPythonAnalysis computes interaction energies from CrystalExplorer data in Mackenzie et al. (2017) using NumPy. GRADE grading scores evidence strength for pharmaceutical claims.

Synthesize & Write

Synthesis Agent detects gaps in mechanochemical scalability from Howard et al. (2018), flags contradictions in halogen bond strengths (Mukherjee et al., 2014), and uses exportMermaid for synthon diagrams. Writing Agent employs latexEditText, latexSyncCitations for Fleischman et al. (2003), and latexCompile for crystal structure reports.

Use Cases

"Analyze energy frameworks for theophylline cocrystals from Trask 2006"

Research Agent → searchPapers('Trask theophylline cocrystal') → Analysis Agent → readPaperContent + runPythonAnalysis (NumPy plot of CE-B3LYP energies from Mackenzie 2017 data) → matplotlib graph of stability enhancement.

"Write LaTeX review of carbamazepine cocrystals with citations"

Research Agent → citationGraph('Fleischman 2003') → Synthesis Agent → gap detection → Writing Agent → latexEditText + latexSyncCitations (13 phases) + latexCompile → PDF with diagrams.

"Find code for cocrystal prediction models in recent papers"

Research Agent → searchPapers('cocrystal prediction model') → Code Discovery → paperExtractUrls → paperFindGithubRepo → githubRepoInspect → Python scripts for synthon screening.

Automated Workflows

Deep Research workflow scans 50+ cocrystal papers via searchPapers, structures reports with GRADE on pharmaceutical impacts (Shan 2008), and synthesizes via DeepScan's 7-step analysis with CoVe checkpoints on Trask 2006 stability data. Theorizer generates hypotheses on halogen-cocrystal synthons from Mukherjee 2014, chaining citationGraph to recent Bolla 2022 advances.

Frequently Asked Questions

What defines crystal engineering of cocrystals?

It designs multicomponent crystals using supramolecular synthons between APIs and coformers to tune properties like solubility.

What are key methods in cocrystal engineering?

Methods include mechanochemistry (Howard et al., 2018), energy frameworks (Mackenzie et al., 2017), and halogen bonding (Mukherjee et al., 2014).

What are seminal papers?

Shan and Zaworotko (2008, 730 citations) on pharmaceutical roles; Fleischman et al. (2003, 530 citations) on carbamazepine phases.

What open problems exist?

Challenges include scalable prediction of formation, synthesis yields, and property modeling beyond hydrogen bonds (Bolla et al., 2022).

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